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EP4140982A3 - Processes and intermediates for the preparations of carboprost and carboprost tromethamine, and carboprost tromethamine prepared therefrom - Google Patents

Processes and intermediates for the preparations of carboprost and carboprost tromethamine, and carboprost tromethamine prepared therefrom Download PDF

Info

Publication number
EP4140982A3
EP4140982A3 EP22186007.5A EP22186007A EP4140982A3 EP 4140982 A3 EP4140982 A3 EP 4140982A3 EP 22186007 A EP22186007 A EP 22186007A EP 4140982 A3 EP4140982 A3 EP 4140982A3
Authority
EP
European Patent Office
Prior art keywords
carboprost
tromethamine
processes
intermediates
preparations
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP22186007.5A
Other languages
German (de)
French (fr)
Other versions
EP4140982B1 (en
EP4140982C0 (en
EP4140982A2 (en
Inventor
Shih-Yi Wei
Min-Kuan Hsu
Jian-Bang Jheng
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chirogate International Inc
Original Assignee
Chirogate International Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chirogate International Inc filed Critical Chirogate International Inc
Priority to EP24223868.1A priority Critical patent/EP4509492A2/en
Publication of EP4140982A2 publication Critical patent/EP4140982A2/en
Publication of EP4140982A3 publication Critical patent/EP4140982A3/en
Application granted granted Critical
Publication of EP4140982B1 publication Critical patent/EP4140982B1/en
Publication of EP4140982C0 publication Critical patent/EP4140982C0/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
    • C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
    • C07C405/0016—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing only hydroxy, etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/46—Unsaturated compounds containing hydroxy or O-metal groups containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to processes for preparing Carboprost or Carboprost Tromethamine, and intermediates prepared from the process, and 5,6-trans isomer free Carboprost or Carboprost Tromethamine prepared therefrom. The invention also relates to a novel crystalline form of Carboprost Tromethamine.
EP22186007.5A 2021-08-23 2022-07-20 Processes and intermediates for the preparations of carboprost and carboprost tromethamine, and carboprost tromethamine prepared therefrom Active EP4140982B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP24223868.1A EP4509492A2 (en) 2021-08-23 2022-07-20 Processes and intermediates for the preparations of carboprost and carboprost tromethamine, and carboprost tromethamine prepared therefrom

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US17/408,864 US20230097470A1 (en) 2021-08-23 2021-08-23 Processes and intermediates for the preparations of carboprost and carboprost tromethamine, and carboprost tromethamine prepared therefrom

Related Child Applications (2)

Application Number Title Priority Date Filing Date
EP24223868.1A Division-Into EP4509492A2 (en) 2021-08-23 2022-07-20 Processes and intermediates for the preparations of carboprost and carboprost tromethamine, and carboprost tromethamine prepared therefrom
EP24223868.1A Division EP4509492A2 (en) 2021-08-23 2022-07-20 Processes and intermediates for the preparations of carboprost and carboprost tromethamine, and carboprost tromethamine prepared therefrom

Publications (4)

Publication Number Publication Date
EP4140982A2 EP4140982A2 (en) 2023-03-01
EP4140982A3 true EP4140982A3 (en) 2023-05-03
EP4140982B1 EP4140982B1 (en) 2025-02-19
EP4140982C0 EP4140982C0 (en) 2025-02-19

Family

ID=83004492

Family Applications (2)

Application Number Title Priority Date Filing Date
EP22186007.5A Active EP4140982B1 (en) 2021-08-23 2022-07-20 Processes and intermediates for the preparations of carboprost and carboprost tromethamine, and carboprost tromethamine prepared therefrom
EP24223868.1A Pending EP4509492A2 (en) 2021-08-23 2022-07-20 Processes and intermediates for the preparations of carboprost and carboprost tromethamine, and carboprost tromethamine prepared therefrom

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP24223868.1A Pending EP4509492A2 (en) 2021-08-23 2022-07-20 Processes and intermediates for the preparations of carboprost and carboprost tromethamine, and carboprost tromethamine prepared therefrom

Country Status (5)

Country Link
US (2) US20230097470A1 (en)
EP (2) EP4140982B1 (en)
JP (1) JP7569097B2 (en)
KR (1) KR20230029527A (en)
CN (1) CN115710209A (en)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008081191A1 (en) * 2007-01-05 2008-07-10 Astrazeneca Pharma India Limited Improved method for the wittig reaction in the preparation of carboprost
US20130190404A1 (en) * 2010-07-21 2013-07-25 Shanghai Techwell Biopharmaceutical Co., Ltd. Crystals of carboprost tromethamine and the preparation method as well as the uses thereof
EP2837621A1 (en) * 2013-08-15 2015-02-18 Chirogate International Inc. Processes for the preparation of isomer free prostaglandins
WO2015048736A1 (en) * 2013-09-30 2015-04-02 Irix Pharmaceuticals, Inc. Novel synthesis routes for prostaglandins and prostaglandin intermediates using metathesis
WO2017093770A1 (en) * 2015-12-01 2017-06-08 CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. Process for the preparation of carboprost and its tromethamine salt

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3728382A (en) * 1970-05-04 1973-04-17 Upjohn Co 15-methyl and 15-ethyl prostaglandin analogs
IL43571A (en) * 1972-11-08 1977-08-31 Pfizer Omega-pentanorprostaglandins and their preparation
DE2632097C2 (en) * 1976-07-16 1985-08-14 Hoechst Ag, 6230 Frankfurt Cyclopentane derivatives, processes for their preparation and medicaments containing them
US4683330A (en) * 1984-03-08 1987-07-28 The Upjohn Company Interphenylene carbacyclin derivatives
EP0232776B1 (en) * 1986-01-24 1990-10-24 Toray Industries, Inc. 2,5,6,7-tetranor-4,8-inter-m-phenylene pgi2 derivatives
CN1136938A (en) 1995-12-28 1996-12-04 苟文丽 Enema 'Xilekang' for treating gynecopathy and preparing process and use thereof
US20100189647A1 (en) 2006-08-10 2010-07-29 Fusako Takayama Experimental Animal As Pathological Model, Method of Producing the Experimental Animal, and Method of Using the Experimental Animal
CN102816099A (en) 2011-06-09 2012-12-12 上海天伟生物制药有限公司 High-purity carboprost tromethamine, and preparation method and application thereof
CN111777537A (en) 2020-07-30 2020-10-16 南京栖云高活医药科技有限公司 Preparation method of prostaglandin analogue

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008081191A1 (en) * 2007-01-05 2008-07-10 Astrazeneca Pharma India Limited Improved method for the wittig reaction in the preparation of carboprost
US20130190404A1 (en) * 2010-07-21 2013-07-25 Shanghai Techwell Biopharmaceutical Co., Ltd. Crystals of carboprost tromethamine and the preparation method as well as the uses thereof
EP2837621A1 (en) * 2013-08-15 2015-02-18 Chirogate International Inc. Processes for the preparation of isomer free prostaglandins
WO2015048736A1 (en) * 2013-09-30 2015-04-02 Irix Pharmaceuticals, Inc. Novel synthesis routes for prostaglandins and prostaglandin intermediates using metathesis
WO2017093770A1 (en) * 2015-12-01 2017-06-08 CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. Process for the preparation of carboprost and its tromethamine salt

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BUNDY G L ET AL: "SYNTHESIS AND BIOLOGICAL ACTIVITY OF PROSTAGLANDIN LACTONES", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 26, no. 8, August 1983 (1983-08-01), pages 1089 - 1099, XP000999619, ISSN: 0022-2623, DOI: 10.1021/JM00362A001 *
MINO R CAIRA ED - MONTCHAMP JEAN-LUC: "Crystalline Polymorphism of Organic Compounds", TOPICS IN CURRENT CHEMISTRY; [TOPICS IN CURRENT CHEMISTRY], SPRINGER, BERLIN, DE, vol. 198, January 1998 (1998-01-01), pages 163 - 208, XP008166276, ISSN: 0340-1022, [retrieved on 19990226], DOI: 10.1007/3-540-69178-2_5 *
TANASE CONSTANTIN ET AL: "Lactones in the Synthesis of Prostaglandins and Prostaglandin Analogs", INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, vol. 22, no. 4, 4 February 2021 (2021-02-04), pages 1572, XP055983291, DOI: 10.3390/ijms22041572 *

Also Published As

Publication number Publication date
US20230097470A1 (en) 2023-03-30
JP2023031276A (en) 2023-03-08
JP7569097B2 (en) 2024-10-17
KR20230029527A (en) 2023-03-03
EP4140982B1 (en) 2025-02-19
US20230131316A1 (en) 2023-04-27
EP4140982C0 (en) 2025-02-19
EP4140982A2 (en) 2023-03-01
CN115710209A (en) 2023-02-24
EP4509492A2 (en) 2025-02-19

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